(S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-acetamidopropanoic acid

Base Information

• Chemical Name: (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-acetamidopropanoic acid
• CAS No.: 181952-29-4
• Molecular Formula: C₂₀H₂₀N₂O₅
• Molecular Weight: 368.389
• Mol file: 181952-29-4.mol

Synonyms:(S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-acetamidopropanoic acid

Chemical Property of (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-acetamidopropanoic acid

Chemical Property:

• Melting Point: 237 °C (decomp)
• Boiling Point: 684.9±55.0 °C(Predicted)
• Density: 1.307±0.06 g/cm3(Predicted)

Purity/Quality:

99.3% ^*data from raw suppliers

Fmoc-Dap(Ac)-OH ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-acetamidopropanoic acid

There total 3 articles about (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-acetamidopropanoic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

acetic anhydride (108-24-7) + 3-amino-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine (181954-34-7) → (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-acetamidopropanoic acid (181952-29-4,1313054-72-6)

Guidance literature:

With pyridine; In tetrahydrofuran; ethyl acetate;

Reference yield:

N-α-tert-butoxycarbonyl-N-β-(9-fluorenylmethoxycarbonyl)-L-diaminopropionic acid (162558-25-0) → (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-acetamidopropanoic acid (181952-29-4,1313054-72-6)

Guidance literature:

Multi-step reaction with 2 steps

1: trifluoroacetic acid / CH₂Cl₂ / 1 h

2: pyridine / 1 h / 25 °C

With pyridine; trifluoroacetic acid; In dichloromethane;

DOI:10.1021/ja0274498

Reference yield:

L-3-acetyl-amino-2-amino-propionic acid (20584-70-7) + (fluorenylmethoxy)carbonyl chloride (28920-43-6) → (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-acetamidopropanoic acid (181952-29-4,1313054-72-6)

Guidance literature:

L-3-acetyl-amino-2-amino-propionic acid; With hydrogenchloride; In methanol; water;

(fluorenylmethoxy)carbonyl chloride; With sodium carbonate; In 1,4-dioxane; water; at 0 - 20 ℃;

DOI:10.1021/jm900629w

upstream raw materials:

acetic anhydride

3-amino-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine

N-α-tert-butoxycarbonyl-N-β-(9-fluorenylmethoxycarbonyl)-L-diaminopropionic acid

L-3-acetyl-amino-2-amino-propionic acid

Downstream raw materials:

NH₂<-Val<-Ala<-Leu<-C₁(Ac)<-Fum-Gly-Gly-Phe-OH

NH₂<-Val<-Leu<-Leu<-C₁(Ac)<-Fum-Gly-Gly-Phe-OH

N-[(1S)-1-[(acetylamino)methyl]-2-(hydroxyamino)-2-oxoethyl]-4'-ethyl-1,1'-biphenyl-4-carboxamide

Refernces

• 1、 -. "Antibacterial agents". Paragraph 0177; 0178. . Retrieved 2015/09/22.
• 2、 -. "ANTIBACTERIAL AGENTS". Page/Page column 83. . Retrieved 2009/01/24.